US5650375A - Synergistic herbicidal compositions - Google Patents

Synergistic herbicidal compositions Download PDF

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Publication number
US5650375A
US5650375A US08/461,718 US46171895A US5650375A US 5650375 A US5650375 A US 5650375A US 46171895 A US46171895 A US 46171895A US 5650375 A US5650375 A US 5650375A
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weight
salts
active substances
herbicides
formula
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Expired - Fee Related
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US08/461,718
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Erwin Hacker
Martin Hess
Hans-Philipp Huff
Hans Schumacher
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Hoechst AG
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Hoechst AG
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Priority to US08/813,367 priority patent/US5872077A/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention is in the field of the crop protection agents which can be employed against monocotyledon and dicotyledon weeds, in particular in the combination of herbicides.
  • Combinations of herbicides have now been found whose action, surprisingly, exceeds the extent which would have been expected taking into account the individual action of the components.
  • the combinations of herbicides, according to the invention therefore allow a surprisingly great reduction in application rate of each of the components.
  • the invention therefore relates to herbicidal compositions which comprise
  • the compound of the formula (I) is known as amidosulfuron and disclosed in EP-A-0,131,258 (U.S. Pat. No. 4,718,937).
  • the active substance is generally formulated as a WP (water-soluble powder) or WDG (water-dispersible granules) and employed in the customary manner in the form of a dilution with water.
  • Particularly suitable growth-regulator-type herbicides are the following:
  • MCPB i.e. 4-(4-chloro-2-methylphenoxy)butanoic acid or salts thereof (for example the sodium salt);
  • 2,4-DB i.e. 4-(2,4-dichlorophenoxy)butanoic acid or salts thereof;
  • dichlorprop i.e. 2-(2,4-dichlorophenoxy)propionic acid or salts thereof or esters thereof,
  • MCPA i.e. 2-(4-chloro-2-methylphenoxy)acetic acid or salts thereof.
  • the abovementioned compounds a) to f) represent standard herbicides which are used post-emergence in a large number of agriculturally used crops for controlling weeds and Cyperaceae. Application rates of 100-3000 g of a.i./ha as individual active substances cover in each case a specific sector of the weed flora.
  • the various compounds are used in the forms of the salts and/or esters (references: cf. "The Pesticide Manual", British Crop Protection Council, 9th Edition 1991 and references cited therein).
  • Dicamba i.e. 3,6-dichloro-2-methoxybenzoic acid (or the salts thereof and esters thereof), is also a widely used herbicidal active substance which is applied analogously to the growth-regulator herbicides.
  • the active substance is mainly used post-emergence (for example, inter alia, in cereals and maize), likewise in the forms of the salts thereof and/or esters thereof (cf. "The Pesticide Manual", already mentioned above).
  • Diflufenican i.e. N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide
  • Diflufenican i.e. N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide
  • It is marketed mostly in the form of finished formulations together with other herbicidal active substances (cf. "The Pesticide Manual", already mentioned above).
  • nitrodiphenyl ethers are the following:
  • bifenox i.e. methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
  • fluorglycofen i.e. carboxymethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate; application as single active substance for example only 5-50 g of a.i./ha pre- and post-emergence in cereals and soya.
  • acifluorfen i.e. 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic acid or salts thereof; application as single active substance for example at a rate of 100-500 g of a.i./ha pre- and post-emergence in soya and cereals.
  • oxyfluorfen i.e. 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-1-ethoxy-2-nitrobenzene; application as single active substance for example at a rate of 100-1000 g of a.i./ha pre- and post-emergence in soya or on areas not under cultivation.
  • lactofen i. e. 1-(ethoxycarbonyl)ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate; application as single active substance for example at a rate of 50-500 g of a.i./ha pre- and post-emergence in soya and cereals.
  • fomesafen i.e. N-methylsulfonyl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide
  • application as single active substance for example at a rate of 50-1000 g of a.i./ha pre- and post-emergence in soya or cereals.
  • Particularly suitable sulfonylureas are the following:
  • sulfonylureas which are employed mainly in cereals, in some cases in potatoes and in grassland for post-emergence control of broad-leaf and grass weeds (for example at a rate of 5-80 g of a.i./ha), for example
  • triasulfuron i.e. 1-[2-(2-chloroethoxy)-phenylsulfonyl]-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea;
  • chlorsulfuron i.e. 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea;
  • tribenuron or tribehuron-methyl i.e. 1-[2-(carboxy- or methoxycarbonyl)phenylsulfonyl]-3-methyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea;
  • thifensulfuron or thifensulfuron-methyl i.e. 1-[2-(carboxy- or methoxycarbonyl)-thiophen-3-yl-sulfonyl]-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea and
  • sulfonylureas which are employed mainly in maize and perennial crops for post-emergence control of grass and broad-leaf weeds (5-80 g of a.i./ha), for example
  • nicosulfuron i.e. 1-[3-(dimethylamino-carbonyl)-pyridin-2-yl-sulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)-urea;
  • DPX-E 9636 i.e. 1-[3-(ethylsulfonyl)-pyridin-2-yl-sulfonyl]-3-(4,6-dimethoxypyrimid-2-yl)-urea;
  • R 4 is iodine or NR 9 R 10 ,
  • R 5 is E, halogen, cyano, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, (C 1 -C 3 -alkoxy)-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy)-carbonyl, mono- or di-(C 1 -C 3 -alkyl)-amino, C 1 -C 3 -alkyl-sulfinyl or -sulfonyl, SO 2 --NR a R b or CO--NR a R b , in particular H,
  • R a and R b independently of one another are H, C 1 -C 3 -alkyl, C 1 -C 3 -alkenyl, C 1 -C 3 -alkynyl, or together are --(CH 2 ) 4 --, --(CH 2 ) 5 -- or --(CH 2 ) 2 --O--(CH 2 ) 2 --,
  • R 6 is H or CH 3 ,
  • R 7 is halogen, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkyl, preferably CF 3 , C 1 -C 2 -haloalkoxy, preferably OCHF 2 or OCH 2 CF 3 ,
  • R 8 is C 1 -C 2 -alkyl, C 1 -C 2 -haloalkoxy, preferably OCHF 2 or C 1 -C 2 -alkoxy, and
  • R 9 is C 1 -C 4 -alkyl and R 10 is C 1 -C 4 -alkylsulfonyl, or R 9 and R 10 together are a chain of the formula --(CH 2 ) 3 SO 2 -- or --(CH 2 ) 4 SO 2 --.
  • DPX-E 9636 is known from Brighton Crop Protection Conference--Weeds--1989, p. 33 et seq.
  • Suitable grass herbicides are mainly the following herbicides for the selective post-emergence control of harmful plants (grass weeds and broad-leaf weeds) in cereals (range of application rates 30 to 1000 g of a.i./ha):
  • diclofop or diclofop-methyl i.e. 2-[4-(2,4-dichlorophenoxy)phenoxy]propionic acid or its methyl ester;
  • tralkoxydim i.e. 2-[1-(ethoxyimino)-propyl]-3-hydroxy-5-mesitylcyclohex, 2-en-1-one;
  • imazamethabenz i.e. a mixture of 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-methyl-benzoic acid and -4-methyl-benzoic acid or their methyl esters;
  • flamprop or flamprop-methyl i.e. N-benzoyl-N-(3-chloro-4-fluorophenyl)-alanine, or its methyl ester;
  • CGA-184927 is known from EP-A-191,736 and Brighton Crop Protection Conference--Weeds--1989.
  • the choice of the ratio by weight and the application rates are a function of, for example, the other component in the mixture, the development stage of the broad-leaf weeds or grass weeds, the weed spectrum, environmental factors and climatic conditions.
  • the ratios by weight A:B of the combined herbicides can therefore vary within wide limits and are generally 1:200 to 20:1.
  • growth-regulator herbicides 1:200 to 2:1, preferably 1:50 to 1:1;
  • dicamba 1:200 to 2:1, preferably 1:50 to 1:1;
  • diflufenican 1:200 to 5:1, preferably 1:50 to 2:1;
  • nitrodiphenyl ethers 1:200 to 10:1, preferably 1:50 to 5:1;
  • grass herbicides 1:200 to 3:1, preferably 1:50 to 10:1.
  • the application rates of B type compounds in the mixtures are generally from 5 to 100 g of a.i./ha, preferably
  • dicamba 50 to 1000 g of a.i./ha
  • diflufenican 20 to 1000 g of a.i./ha
  • nitrodiphenyl ethers 10 to 1000 g of a.i./ha
  • grass herbicides 30 to 1000 g of a.i./ha.
  • the active substance combinations according to the invention can exist as mixed formulations of the two components which are then applied in the customary manner in the form of a dilution with water, or are prepared in the form of so-called tank mixes by concomitant dilution of the separately formulated components with water.
  • the A type and B type compounds or their combinations can be formulated in many ways, depending on the prevailing biological and/or chemicophysical parameters.
  • WP wettable powders
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • EW emulsions
  • DP dusting powders
  • WG water-dispersible granules
  • ULV formulations micro-capsul
  • Wettable powders are preparations which can be dispersed uniformly in water and which comprise, beside the active substance, ionic or non-ionic surfactants (wetting agents, dispersants), for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutyl-naphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance.
  • ionic or non-ionic surfactants for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, fatty alcohol polyglycol ether s
  • Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else higher-boiling aromatics or hydrocarbons, with the addition of one or more ionic or non-ionic surfactants (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene, or else higher-boiling aromatics or hydrocarbons.
  • emulsifiers which can be used: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condsensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethytene sorbitol esters.
  • calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
  • non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condsensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxy
  • Dusting powders are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carrier substances such as sand, kaolinites or granulated inert material with the aid of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else nineral oils.
  • Suitable active substances can also be granulated in the fashion customary for the preparation of fertilizer granules, if desired in the form of a mixture with fertilizers.
  • Water-dispersible granules are generally prepared by methods such as spray-drying, fluidized-bed granulation, disk granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations comprise 0.1 to 99% by weight, in particular 2 to 95% by weight, of active substances of types A+B.
  • concentrations of the active substances A+B can differ in the formulations.
  • the active substance concentration in wettable powders is approximately 10 to 95% by weight, the remainder to 100% by weight is composed of customary formulation components.
  • the active substance concentration can be approximately 1 to 85% by weight, preferably 5 to 80% by weight.
  • Formulations in the form of dusts comprise approximately 1 to 25% by weight, usually 5 to 20% by weight, of active substance, sprayable solutions approximately 0.2 to 25% by weight, preferably 2 to 20% by weight, of active substance.
  • the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries and fillers are used. The content in the case of the water-dispersible granules is generally between 10 and 90% by weight.
  • the active substance formulations mentioned optionally comprise the adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors, pH regulators and viscosity regulators which are customary in each case.
  • the formulations which exist in commercially available form are optionally diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules.
  • Preparations in the form of dusts, granules for soil application or for broadcasting as well as sprayable solutions are customarily not diluted further with other inert substances before application.
  • the active substances can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation.
  • the active substances are preferably applied jointly in the form of tank mixes, the optimally formulated concentrated formulations of the single active substances being mixed concomitantly with water in the tank, and the spray mixture obtained is applied.
  • a dusting agent is obtained by mixing 10 parts by weight of an active substance combination according to the invention and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substances A+B, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active substances A+B with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, approx. 255° to 277° C.), and grinding the mixture in a ball mill to a fineness of below 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.
  • Water-dispersible granules are obtained by mixing 75 parts by weight of active substances A+B, 10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, grinding the mixture on a pinned disk mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.
  • water-dispersible granules are obtained by homogenizing and precomminuting 25 parts by weight of active substances A+B, 5 parts by weight of sodium2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water on a colloid mill, subsequently grinding the mixture on a bead mill, and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.
  • the herbicidal activity of the treated plots was assessed by comparison with untreated control plots by visual scoring.
  • the herbicidal action as regards influencing the plant growth and chlorotic and necrotic effects up to the total destruction of the weeds was assessed qualitatively and quantitatively and indicated as percentage action (0-100%).
  • the crop tolerance, assessed in the form of damage, is not adversely affected, i.e. the combinations can be judged as fully selective.

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Epoxy Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
US08/461,718 1991-07-12 1995-06-05 Synergistic herbicidal compositions Expired - Fee Related US5650375A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US08/461,718 US5650375A (en) 1991-07-12 1995-06-05 Synergistic herbicidal compositions
US08/813,367 US5872077A (en) 1991-07-12 1997-03-07 Synergistic herbicidal compostitions

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4123111.2 1991-07-12
DE4123111 1991-07-12
US91024592A 1992-07-09 1992-07-09
US19966794A 1994-02-22 1994-02-22
US08/461,718 US5650375A (en) 1991-07-12 1995-06-05 Synergistic herbicidal compositions

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US19966794A Continuation 1991-07-12 1994-02-22

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US08/813,367 Division US5872077A (en) 1991-07-12 1997-03-07 Synergistic herbicidal compostitions

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US08/461,718 Expired - Fee Related US5650375A (en) 1991-07-12 1995-06-05 Synergistic herbicidal compositions
US08/813,367 Expired - Fee Related US5872077A (en) 1991-07-12 1997-03-07 Synergistic herbicidal compostitions

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US08/813,367 Expired - Fee Related US5872077A (en) 1991-07-12 1997-03-07 Synergistic herbicidal compostitions

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US (2) US5650375A (de)
EP (4) EP0807381B1 (de)
JP (1) JPH05194124A (de)
CN (2) CN1046184C (de)
AT (4) ATE143767T1 (de)
AU (1) AU650552B2 (de)
BR (1) BR9202574A (de)
CA (1) CA2073597A1 (de)
CZ (1) CZ285462B6 (de)
DE (4) DE59207323D1 (de)
DK (4) DK0807381T3 (de)
ES (3) ES2147816T3 (de)
GR (1) GR3021317T3 (de)
HU (1) HU212259B (de)
IE (2) IE20010221A1 (de)
MX (1) MX9204083A (de)
PL (5) PL172183B1 (de)
PT (2) PT807381E (de)
RO (1) RO117587B1 (de)
RU (2) RU2083107C1 (de)
SK (1) SK216192A3 (de)
TR (1) TR28811A (de)
ZA (1) ZA925164B (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020042345A1 (en) * 2000-05-11 2002-04-11 Jean Kocur Combination of crop protection agents with hydrogen bond-forming polymers
US6559098B1 (en) * 1997-02-05 2003-05-06 Basf Aktiengesellschaft Sulphonylurea and/adjuvant based solid mixtures
US20030186816A1 (en) * 2002-03-05 2003-10-02 Bayer Cropscience Gmbh Herbicide combinations comprising specific sulfonylureas
US20050026786A1 (en) * 2003-07-28 2005-02-03 Bayer Cropscience Gmbh Oil suspension concentrate
US7056863B1 (en) 1999-10-22 2006-06-06 Aventis Cropscience Gmbh Synergistic herbicidal compositions herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors
US20060234863A1 (en) * 2003-02-19 2006-10-19 Hans-Peter Krause Method for producing water-dispersible granules
WO2007033759A1 (de) * 2005-09-16 2007-03-29 Bayer Cropscience Ag Festformulierung
US20090156400A1 (en) * 2001-07-21 2009-06-18 Herbicide combinations comprising specific sulfonylureas
US20090229006A1 (en) * 1996-11-07 2009-09-10 Syngenta Ag Herbicide resistant plants

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0569944B1 (de) * 1992-05-15 1999-03-31 Hoechst Schering AgrEvo GmbH Synergistisch wirksame Herbizidkombinationen
AU6996494A (en) * 1993-05-26 1994-12-20 Sandoz Ltd. Herbicidal compositions
KR100314469B1 (ko) * 1993-09-14 2002-11-23 노바르티스아게 제초제 조성물
CZ291924B6 (cs) 1994-12-22 2003-06-18 Monsanto Company Herbicidní kompozice obsahující derivát sulfonylmočoviny
DE19520839A1 (de) * 1995-06-08 1996-12-12 Hoechst Schering Agrevo Gmbh Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern
TWI243019B (en) * 2000-08-31 2005-11-11 Basf Ag Process for the preparation of a solid herbicidal formulation
DE10135641A1 (de) * 2001-07-21 2003-02-06 Bayer Cropscience Gmbh Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen
AU2002342721A1 (en) * 2001-09-20 2003-04-01 Syngenta Participations Ag Herbicidal composition
AR036580A1 (es) * 2001-09-27 2004-09-15 Syngenta Participations Ag Composicion herbicida
DE10209468A1 (de) * 2002-03-05 2003-09-18 Bayer Cropscience Gmbh Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen
CN102711469A (zh) * 2009-11-13 2012-10-03 陶氏益农公司 含有氯氨吡啶酸和磺酰脲的协同除草组合物
CN102302007B (zh) * 2011-07-01 2014-06-18 陕西美邦农药有限公司 一种含吡氟酰草胺与磺酰脲类的除草组合物
CN105165866B (zh) * 2013-07-03 2017-08-08 江苏龙灯化学有限公司 增效除草组合物
CN104396954A (zh) * 2014-03-29 2015-03-11 潍坊先达化工有限公司 含有2,4-二氯苯氧丁酸及其衍生物的除草剂组合物
CN105360148A (zh) * 2015-07-22 2016-03-02 南京华洲药业有限公司 一种含炔草酯与酰嘧磺隆的复合除草组合物及其应用
CN108338177A (zh) * 2017-12-26 2018-07-31 安徽省农业科学院植物保护与农产品质量安全研究所 一种含三甲苯草酮与酰嘧磺隆的除草组合物

Citations (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863753A (en) * 1954-07-06 1958-12-09 Nat Res Dev Method of weed control
US3961935A (en) * 1972-11-10 1976-06-08 Sumitomo Chemical Company, Limited Synergistic herbicidal composition comprising O-methyl or O-ethyl-O-(3-methyl-6-nitrophenyl)-N-secondary-butylphosphorothioamidate and a phenoxy-type herbicide
JPS58192808A (ja) * 1982-04-28 1983-11-10 Nippon Tokushu Noyaku Seizo Kk 除草剤
US4460402A (en) * 1981-07-10 1984-07-17 Rhone-Poulenc Agrochimie Synergistic herbicide compositions of phenoxybenzoic acids and cyclohexanediones
EP0120578A2 (de) * 1983-02-15 1984-10-03 Rohm And Haas France, S.A. Herbizide Zusammensetzungen und deren Verwendung zur Bekämpfung unerwünschten Unkrauts
GB2137092A (en) * 1983-02-28 1984-10-03 Ici Plc Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops
EP0131258A2 (de) * 1983-07-09 1985-01-16 Hoechst Aktiengesellschaft Neue N-Alkoxy- N-Alkylsulfonylaminosulfonylharnstoffe, und neue (Pyrimido) Triazino-thiatriazinoxide als Vorprodukte
JPS6157505A (ja) * 1984-08-29 1986-03-24 Nissan Chem Ind Ltd 除草剤組成物
EP0210818A1 (de) * 1985-07-23 1987-02-04 May & Baker Limited Verfahren zur Unkrautbekämpfung mit Verwendung von Diflufenican
US4690706A (en) * 1973-04-17 1987-09-01 Basf Aktiengesellschaft Herbicide
EP0236273A2 (de) * 1986-03-07 1987-09-09 Ciba-Geigy Ag Synergistisches Mittel und Verfahren zur selektiven Unkrautbekämpfung in Getreide
EP0248968A1 (de) * 1986-06-12 1987-12-16 Ciba-Geigy Ag (R)-2-[4-(5-Chlor-3-fluorpyridin-2-yloxy)-phenoxy]-propionsäure-propinylester mit herbizider Wirkung
EP0252237A2 (de) * 1986-05-09 1988-01-13 Hoechst Aktiengesellschaft Herbizide Mittel
EP0273668A2 (de) * 1986-12-23 1988-07-06 May & Baker Limited Herbizides Verfahren mit Verwendung von Diflufenican
EP0298901A2 (de) * 1987-07-10 1989-01-11 Hoechst Aktiengesellschaft Herbizide Mittel
EP0303383A2 (de) * 1987-08-10 1989-02-15 Ishihara Sangyo Kaisha, Ltd. Herbizide Zusammensetzung
EP0324302A1 (de) * 1988-01-12 1989-07-19 Rhone-Poulenc Agrochimie Synergistische herbizide Mischung auf der Basis von Bifenox und Metsulfuron-Methyl
AU587549B2 (en) * 1986-05-28 1989-08-17 Crop Care Australasia Pty Ltd Improved herbicide combinations
EP0341011A1 (de) * 1988-05-03 1989-11-08 E.I. Du Pont De Nemours And Company Herbizide Pyridinsulfonylharnstoffe
EP0401677A2 (de) * 1989-06-05 1990-12-12 Hoechst Aktiengesellschaft Herbizide Mittel
EP0401678A1 (de) * 1989-06-05 1990-12-12 Hoechst Aktiengesellschaft Herbizide Mittel
WO1991010660A1 (de) * 1990-01-10 1991-07-25 Hoechst Aktiengesellschaft Pyridylsulfonylharnstoffe als herbizide und pflanzenwachstumsregulatoren, verfahren zu ihrer herstellung und ihre verwendung
US5236887A (en) * 1991-05-03 1993-08-17 Dowelanco Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-d below a ph of 5
US5478795A (en) * 1987-01-09 1995-12-26 American Cyanamid Company Synergistic herbicidal imidazolinone compositions

Patent Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863753A (en) * 1954-07-06 1958-12-09 Nat Res Dev Method of weed control
US3961935A (en) * 1972-11-10 1976-06-08 Sumitomo Chemical Company, Limited Synergistic herbicidal composition comprising O-methyl or O-ethyl-O-(3-methyl-6-nitrophenyl)-N-secondary-butylphosphorothioamidate and a phenoxy-type herbicide
US4690706A (en) * 1973-04-17 1987-09-01 Basf Aktiengesellschaft Herbicide
US4460402A (en) * 1981-07-10 1984-07-17 Rhone-Poulenc Agrochimie Synergistic herbicide compositions of phenoxybenzoic acids and cyclohexanediones
JPS58192808A (ja) * 1982-04-28 1983-11-10 Nippon Tokushu Noyaku Seizo Kk 除草剤
EP0120578A2 (de) * 1983-02-15 1984-10-03 Rohm And Haas France, S.A. Herbizide Zusammensetzungen und deren Verwendung zur Bekämpfung unerwünschten Unkrauts
GB2137092A (en) * 1983-02-28 1984-10-03 Ici Plc Phenoxypropionic Acid Derivatives for Selective Herbicides in Rice Crops
US4718937A (en) * 1983-07-09 1988-01-12 Hoechst Aktiengesellschaft N-alkoxyaminosulfonylureas and N-alkylsulfonylaminosulfonylureas
EP0131258A2 (de) * 1983-07-09 1985-01-16 Hoechst Aktiengesellschaft Neue N-Alkoxy- N-Alkylsulfonylaminosulfonylharnstoffe, und neue (Pyrimido) Triazino-thiatriazinoxide als Vorprodukte
JPS6157505A (ja) * 1984-08-29 1986-03-24 Nissan Chem Ind Ltd 除草剤組成物
EP0210818A1 (de) * 1985-07-23 1987-02-04 May & Baker Limited Verfahren zur Unkrautbekämpfung mit Verwendung von Diflufenican
EP0236273A2 (de) * 1986-03-07 1987-09-09 Ciba-Geigy Ag Synergistisches Mittel und Verfahren zur selektiven Unkrautbekämpfung in Getreide
EP0252237A2 (de) * 1986-05-09 1988-01-13 Hoechst Aktiengesellschaft Herbizide Mittel
AU587549B2 (en) * 1986-05-28 1989-08-17 Crop Care Australasia Pty Ltd Improved herbicide combinations
EP0248968A1 (de) * 1986-06-12 1987-12-16 Ciba-Geigy Ag (R)-2-[4-(5-Chlor-3-fluorpyridin-2-yloxy)-phenoxy]-propionsäure-propinylester mit herbizider Wirkung
EP0273668A2 (de) * 1986-12-23 1988-07-06 May & Baker Limited Herbizides Verfahren mit Verwendung von Diflufenican
US5478795A (en) * 1987-01-09 1995-12-26 American Cyanamid Company Synergistic herbicidal imidazolinone compositions
EP0298901A2 (de) * 1987-07-10 1989-01-11 Hoechst Aktiengesellschaft Herbizide Mittel
EP0303383A2 (de) * 1987-08-10 1989-02-15 Ishihara Sangyo Kaisha, Ltd. Herbizide Zusammensetzung
EP0324302A1 (de) * 1988-01-12 1989-07-19 Rhone-Poulenc Agrochimie Synergistische herbizide Mischung auf der Basis von Bifenox und Metsulfuron-Methyl
EP0341011A1 (de) * 1988-05-03 1989-11-08 E.I. Du Pont De Nemours And Company Herbizide Pyridinsulfonylharnstoffe
EP0401677A2 (de) * 1989-06-05 1990-12-12 Hoechst Aktiengesellschaft Herbizide Mittel
EP0401678A1 (de) * 1989-06-05 1990-12-12 Hoechst Aktiengesellschaft Herbizide Mittel
WO1991010660A1 (de) * 1990-01-10 1991-07-25 Hoechst Aktiengesellschaft Pyridylsulfonylharnstoffe als herbizide und pflanzenwachstumsregulatoren, verfahren zu ihrer herstellung und ihre verwendung
US5236887A (en) * 1991-05-03 1993-08-17 Dowelanco Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-d below a ph of 5
US5236887B1 (en) * 1991-05-03 1996-04-16 Dowelanco Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-d below a ph of 5

Non-Patent Citations (21)

* Cited by examiner, † Cited by third party
Title
Blair et al., "A Review of Activity, Fate and Mode of Action of Sulfonylurea Herbicides," Pesticide Science, vol. 22, No. 3 (1988), pp. 195-219.
Blair et al., A Review of Activity, Fate and Mode of Action of Sulfonylurea Herbicides, Pesticide Science, vol. 22, No. 3 (1988), pp. 195 219. *
Chemical Patents Index, Basic Abstracts Journal, Week 8351, Feb. 22, 1984, An 83 847153/51 & JP A 58 192 808, Nov. 10, 1983. *
Chemical Patents Index, Basic Abstracts Journal, Week 8351, Feb. 22, 1984, An 83-847153/51 & JP-A-58 192 808, Nov. 10, 1983.
Chemical Patents Index, Basic Abstracts Journal, Week 8618, Jun. 25, 1986, AN 86 116638/18 & JP A 61 057 505, Mar. 24, 1986. *
Chemical Patents Index, Basic Abstracts Journal, Week 8618, Jun. 25, 1986, AN 86-116638/18 & JP-A-61 057 505, Mar. 24, 1986.
Cramp et al., "Design and Synthesis of N-(2,4-difluorophenyl)-2(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (diflufenican), a Novel Pre-and Early Post-Emergence Herbicide for Use in Winter Cereals," Pesticide Science, vol. 18, No. 1 (1987), pp. 15-28.
Cramp et al., Design and Synthesis of N (2,4 difluorophenyl) 2(3 trifluoromethylphenoxy) 3 pyridinecarboxamide (diflufenican), a Novel Pre and Early Post Emergence Herbicide for Use in Winter Cereals, Pesticide Science, vol. 18, No. 1 (1987), pp. 15 28. *
Devine et al., "Inhibition of Acetolactate Synthase in Susceptible and Resistant Biotypes of Stellaria media," Pesticide Science, vol. 31, No. 3 (1991), pp. 273-280.
Devine et al., Inhibition of Acetolactate Synthase in Susceptible and Resistant Biotypes of Stellaria media, Pesticide Science, vol. 31, No. 3 (1991), pp. 273 280. *
O Sullivan et al., Chlorsulfuron Reduced Control of Wild Oats (Avena Fatua) with Diclofop, Difenzoquat and Flamprop, Weed Science, vol. 32, No. 3 (1984), pp. 285 289. *
O'Sullivan et al., "Chlorsulfuron Reduced Control of Wild Oats (Avena Fatua) with Diclofop, Difenzoquat and Flamprop," Weed Science, vol. 32, No. 3 (1984), pp. 285-289.
The Agrochemicals Handbook, 2nd edition, The Royal Society of Chemistry, Nottingham, England, 1987, p. A926. *
The Pesticide Manual (Incorporating The Agrochemicals Handbook), 10th Edition, 1994, pp. 638 644, pp. 271 273. *
The Pesticide Manual (Incorporating The Agrochemicals Handbook), 10th Edition, 1994, pp. 638-644, pp. 271-273.
Warner, et al., "Tralkoxydim --A New Post-Emergence Cereal Selective Grainicide," Proceedings -British Crop Protection Conference -Weeds (1987), pp. 19-26.
Warner, et al., Tralkoxydim A New Post Emergence Cereal Selective Grainicide, Proceedings British Crop Protection Conference Weeds (1987), pp. 19 26. *
Wightman et al., "The Mode of Action and Basis of Selectivity of Diflufenican in Wheat, Barley and Selected Weed Species," Proceedings -British Crop Protection Conference -Weeds (1985), pp. 171-178.
Wightman et al., The Mode of Action and Basis of Selectivity of Diflufenican in Wheat, Barley and Selected Weed Species, Proceedings British Crop Protection Conference Weeds (1985), pp. 171 178. *
Zollinger et al., "Antagonism Between Selected Postemergence Herbicides for Grass and Broadleaved Weeds," Proceedings of the Western Society of Weed Science, vol. 37 (1984), pp. 167-171.
Zollinger et al., Antagonism Between Selected Postemergence Herbicides for Grass and Broadleaved Weeds, Proceedings of the Western Society of Weed Science, vol. 37 (1984), pp. 167 171. *

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* Cited by examiner, † Cited by third party
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US20090229006A1 (en) * 1996-11-07 2009-09-10 Syngenta Ag Herbicide resistant plants
US6559098B1 (en) * 1997-02-05 2003-05-06 Basf Aktiengesellschaft Sulphonylurea and/adjuvant based solid mixtures
US7056863B1 (en) 1999-10-22 2006-06-06 Aventis Cropscience Gmbh Synergistic herbicidal compositions herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors
US20020042345A1 (en) * 2000-05-11 2002-04-11 Jean Kocur Combination of crop protection agents with hydrogen bond-forming polymers
US20090156400A1 (en) * 2001-07-21 2009-06-18 Herbicide combinations comprising specific sulfonylureas
US20030186816A1 (en) * 2002-03-05 2003-10-02 Bayer Cropscience Gmbh Herbicide combinations comprising specific sulfonylureas
US20080287296A1 (en) * 2002-03-05 2008-11-20 Bayer Cropscience Ag Herbicide Combinations Comprising Specific Sulfonylureas
US20060234863A1 (en) * 2003-02-19 2006-10-19 Hans-Peter Krause Method for producing water-dispersible granules
US20050026786A1 (en) * 2003-07-28 2005-02-03 Bayer Cropscience Gmbh Oil suspension concentrate
WO2007033759A1 (de) * 2005-09-16 2007-03-29 Bayer Cropscience Ag Festformulierung
US8198214B2 (en) 2005-09-16 2012-06-12 Bayer Cropscience Ag Solid formulation

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